Etynodiol

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Etynodiol, or ethynodiol, is a steroidal progestin of the 19-nortestosterone group which was never marketed.[1][2][3] A diacylated derivative, etynodiol diacetate, is used as a hormonal contraceptive.[1][2] Etynodiol is sometimes used as a synonym for etynodiol diacetate.

It was patented in 1955.[4]

Pharmacology

Etynodiol is a prodrug of norethisterone, and is converted immediately and completely into norethisterone.[5][6][7] Etynodiol is an intermediate in the conversion of the prodrug lynestrenol into norethisterone.[8]

Template:Relative affinities of norethisterone, metabolites, and prodrugs

Chemistry

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Etynodiol is a 19-nortestosterone derivative. Structurally, it is almost identical to norethisterone and lynestrenol, differing only in its C3 substituent. Whereas norethisterone has a ketone at C3 and lynestrenol has no substituent at C3, etynodiol has a hydroxyl group at the position.

Synthesis

File:Ethynodiol diacetate synthesis.svg
Ethynodiol diacetate synthesis:[9] F. B. Colton, U.S. patent 2843609 (1958 to Searle). Prepn of the 3-acetate, 17-acetate, and diacetate: P. D. Klimstra, U.S. patent 3176013 (1965 to Searle); see also:[10]

Society and culture

Generic names

Etynodiol is the generic name of the drug and its INNTooltip International Nonproprietary Name, while ethynodiol is its BANTooltip British Approved Name.[1][2]

References

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Template:Progesterone receptor modulators Template:Estrogen receptor modulators Template:Androgen receptor modulators